As we've grown Stripe, we've constantly lamented about how hard it
is to get actionable advice on the specific issues we're dealing
with. As an experiment, we've decided to try out a startup advice
column to share what we've learned along the way.

For this first advice post, I'll respond to an email one of my
(apparently prescient) friends recently sent me.

Hey Greg,

We're spinning up our recruitment engine and are working on our cold
reach out email copy.

Do you have any examples of successful emails you've used in the past
that you'd be willing to share or any advice on the process?

I've actually sent quite a lot of outbound cold emails and A/B
tested until I found a formula that works for me. Cold outreach is
inherently hard because the people you most want to reach will
already receive many of these sollicitations, and you
correspondingly need to differentiate. Here are the main lessons
that I've taken away from my cold pings:

Include
a proof-of-work.
Most cold emails are mechanically assembled: either they're totally
copy-paste, or they substitute in strings (such as your language of
choice) that could be pulled from the Github API. Instead, make sure
your emails include something that proves you've done some work
investigating the person and understanding them. Make an intelligent
comment about one of their talks, or include a suggestion for one of
their projects. (Unfortunately, this doesn't mean you should send
people a crafted hash.)

Don't explain what your company does. Either they've heard of
you, in which case the explanation isn't very useful, or they
haven't, in which case the explanation isn't going to read any
different from the various other emails they get. It also makes you
sound small-time: Google would never send someone an email saying "I
work at Google, a search company in Mountain View which is
organizing the world's information".

Always have the ping come from a non-recruiter. There's
actually nothing wrong with contacts from recruiters generally: good
ones know how to make a candidate feel at ease. In the specific case
of cold pings, you need to make sure that it comes from someone for
whom that email isn't a normal part of their job. It's much better
as a recipient to realize that someone has taken time out of their
day just to contact you, rather than someone simply fulfilling their
quota.

Say the bare minimum required to get a face-to-face chat. No
matter what great information you include in your email, any selling
you do verbally (if they're local, get coffee; otherwise video chat
tends to be way better than phone) will be astronomically more
effective and convincing. So any non-vital detail can really only
serve to shoot you in the foot.

Track response rates. Ultimately these contacts are about
personal style, and it's important to find something that works with
you. I have a Hackpad I use to
record every cold ping I sent, and go back and update it if I get a
reply.

That's a lot of principle, but it compiles down to a very short
email template. Here's a concrete example of one I've used in the
past:

Hey XX,

I'm an engineer at Stripe. I came across your XX post, and it reminded
me of the time that XX. I wanted to see if you'd be interested in working with
us at Stripe — if you're up for it, I'd love to grab coffee next week
to chat.

- gdb

Good luck with the recruiting. Let me know how it turns out!

Have something we can help with? Just send me an email at
gdb@stripe.com with a concrete
question you're facing at your company. It can be related to
anything startup related (technical, managerial, etc). If there's
enough demand, someone from Stripe will regularly (starting out with
every two weeks) respond to a selected email with a post here.